Get All Sentimental
by Lolsome-o-sis girl
Summary: [Dean/Jimmy (Cas)] Jimmy Novak splits his time between going to college in his hometown of Pontiac and dressing up as his alter ego Castiel to sing in front of hundreds upon hundreds of people. How the hell no one has found out yet, he has no idea. He also had no idea about how much of an ass hat Sam's older brother actually was.
1. It's Just A Song

**Get All Sentimental**

 _Fandom: Supernatural_

 _Rating: T_

 _Genre: Humor, Romance_

 _Pairing: Dean/Jimmy (Castiel), Sam/Gabriel_

 _Summary: [Dean/Jimmy (Cas)] Jimmy Novak splits his time between going to college in his hometown of Pontiac and dressing up as his alter ego Castiel to sing in front of hundreds upon hundreds of people. How the hell no one has found out yet, he has no idea. He also had no idea about how much of an ass hat Sam_ _'s older brother actually was._

* * *

 **AN: Yes. This** **is real. Buckle up, sock puppets.**

 **This is the first in a series of cheesy Disney AUs. I have four planned so far, but there could be more than that, if people want me to and I think of any others that I could do.**

 **Thank you masterofmadness, for accepting the phrase "Hannah Montana AU" with grace and poise.**

 **As always, enjoy :) X.**

 **DISCLAIMER. I own nothing.**

* * *

 _ **1.**_ _It's Just A Song_

Sometimes, Jimmy Novak wishes that he was still a child.

Now that he's technically a responsible (apparently) adult, Chuck, his father, has decided that his youngest son is old enough to start making his own life choices. Which is, in Jimmy's opinion, a terrible idea. Most of the time, he can't even decide what he wants for breakfast in the morning, never mind important, crucial decisions that will affect the future of his career for the next for-fucking-ever. He really should have planned ahead when taking on this whole double life/secret identity thing.

Of course, when he had started, no one had really predicted what was going to happen. Jimmy was just a sixteen year old sophomore who liked to sing in the locker room after gym class, when everybody else had filtered out for the day. It wasn't his fault that someone, namely Luke, his older brother, had heard him and recruited the rest of the family to start spying on him in case he broke out into song, and _they_ had set the wheels in motion. Jimmy, being cripplingly shy at the time, had all but refused to even step foot within a ten mile radius of a recording studio, even if there was the very likely possibility that nothing would ever come of it, which had led Chuck to suggest the idea of Castiel, the alter ego that no one would see through. Jimmy liked the idea at first, but, now, he was realising that he was kind of stuck with the guy, stuck with the fake stubble and the gruff voice.

Even so, how on earth no one has seen through him yet, he has no idea. He only has to take his glasses off and run his fingers through his hair to mess it up a little, and he looks almost exactly like he does when he's being Castiel, just without the stubble. Yet here he is, sitting in the cafeteria, studying from the electronic textbook he's downloaded onto his tablet, waiting for his friends to show up, just like everybody else.

Speaking of which -

"Jimmy!"

The sound of a familiar voice breaks his concentration. He glances up from the screen, glasses sliding down his nose as he does so, only to see Meg sliding into the seat beside him, closely followed by Amelia and Sam.

"Hey," he greets, adjusting his glasses. "Where's Gabe?"

"Who knows. Probably running around taking photos for his big photography brief." Sam rolls his eyes fondly at the mention of Gabe. "You know what he's like about all of that stuff."

"I've had nineteen years of that ass hat, so, yeah, I do." Jimmy rolls his eyes too. Sam _adores_ Gabe, sometimes to the point of stupidity, in Jimmy's opinion; they're so sickeningly sweet to each other, it's boarding on tooth-rotting.

Meg taps her nails on the table, as she rips the plastic wrap off her salad. Clearly, her topic of conversation is more important than the topic of Jimmy's brother's whereabouts.

"Did you guys hear Castiel on the radio this morning?"

Amelia groans, looking like she's barely resisting the urge to smack her head against the tabletop. "God, please, not this _again_."

"Not what again?" Jimmy asks, feigning ignorance.

"Castiel's new song dropped on the radio this morning," Sam explains, gesturing to their mutual friend, "and Meg hasn't shut up about it."

"Hey!" She aims a shove at him across the table. "Don't you dare start attacking my unicorn; If it was your brother's song on the radio, you'd be just the same!"

"She's got a point," Jimmy says. None of them have actually met Dean, Sam's older brother, but his career had taken off a few years ago, only a year or so before Castiel's had, and now there are people out there who swoon when they even hear his name. From what Jimmy could remember from those early freshman days, Sam had been in high school at the time, and had been smothered from that point on. When they had all gotten to college, the guy had decided to forgo using his real name, enrolling himself as Sam Wesson to avoid being hassled.

"It's not that I'm not proud to be his brother," he said, at the time, when the others had questioned him about it. "I wouldn't change having Dean as my brother - or Adam, for that matter - for anything in the world, but it would be nice to be able to go to class without having someone come up to me and ask if I can get them Dean's autograph."

Jimmy had been in no position to judge that reasoning, after all. That's exactly the reason why, in the space of his three-year career, his double life has remained a secret to everyone outside of the family.

Amelia sniffs. "I don't see why you're getting so worked up over this." She tears off a chunk of her sandwich, as if to prove some kind of point. "It's just a song."

" _ **Excuse me?**_ " Meg almost sends her mouthful of salad spiralling across the table. Jimmy's debating whether or not to take cover for the rest of this conversation. Meg has been essentially _in love_ with Castiel for the past two years, and he's not sure whether to feel flattered or fucking terrified by her fierce loyalty. "It is not _just a song_. It's an _anthem_ , a classic. It's about the person you are on the inside, about letting it shine through; it's about someone, a person you care about, seeing the real you, not the act that we present to the world."

Jimmy raises an eyebrow. "Wow. That's deep." Deeper than what he was thinking when he _wrote_ that song; he was just pissed off that he had overheard someone talking shit about him one day on the way home, prompting him to throw down his feelings into lyrical form.

Amelia and Sam both snort simultaneously.

"Uh hu," the redhead says, causing Meg to pout. " _Sure_ it is."

The brunette glares at her. "When I'm living in a mansion with my soulmate, you will all be sorry you mocked his musical genius."

" _Soulmate?_ " Jimmy repeats, trying to keep a straight face.

"Yes, Jimmy. _Soulmate_."

Sam and Amelia simply laugh, before quickly moving onto another topic of conversation before Meg can carry on talking about Castiel, her _unicorn_. Which Jimmy is incredibly grateful for; Meg has been his friend for a long time, but the idea of the two of them being soulmates is a little...unnerving, to put it nicely. He often finds himself wondering how Meg would ever react if she did find out that one of her best friends is, in fact, her "soulmate" - and, more often than not, finds himself pushing that idea to one side, because the answer usually involves him being murdered, if not gravely injured, in the wake of Meg's wrath.

And, true to her fangirl spirit, Meg isn't deterred by Sam and Amelia's changing of the subject. She still does not keep quiet about Castiel throughout that afternoon, muttering to Jimmy all the way through their New Media seminar, and all the way to her car, where Gabe and the others are waiting for them at the end of the day. They'd all decided to spend the evening at Sam's place, and Meg had been nominated the driver; Gabe had offered, but Jimmy quickly voted against the idea, for Gabe's driving skills are not the best in the world. Not that Meg is really any safer; she slams her foot on the gas as soon as the passenger doors are shut, switching on the radio and turning the volume up when she hears Castiel's new song come on. Jimmy tries to hide his wince at hearing his Castiel voice through the speakers, whilst Amelia makes a face from the back seat at having to hear it at all, but Meg merely sticks her tongue out at the redhead's reflection in the rear-view mirror, making sure to scream " _ **I'm unusual, not so typical**_ " louder than she perhaps would have done otherwise.

They camp outside on the front lawn when they make it to the Winchester household, not even bothering to venture inside, wanting to make the most of the slightly warm autumnal weather before it vanishes. Sam tries to read about three Pre-Law books at the same time, causing Gabe to laugh and wrap a comforting arm around him, whilst Amelia and Meg chat amongst themselves, but Jimmy's brain won't focus on the New Media thesis he's been given; instead, he's tapping his pencil lightly against the empty page of his notebook, trying to work out the lyrics to some melody only he can hear.

 _So what you see, is only half the story, there's another side of me._

 _Don't want to be, treated differently,_

 _I want to keep it all inside._

"What's that?" Sam's trying to see what he's scribbling; Jimmy almost rips the page out of the notebook in his haste to hide it.

"Nothing," he says quickly. "Just, er - just some stuff I have to remember. No big deal, really." He switches to a safer topic of conversation. "How's Pre-Law going?"

Sam sighs heavily, Jimmy's list of "some stuff" forgotten, thankfully. "How do you think it's going?"

"Aw, don't look like that, Samsquatch." Gabe nuzzles the top of Sam's head. "You'll smash it, just like you do every assignment that you turn in."

"I know." Sam drops the book currently in his hands, glancing out into the distance, his eyes following the curve of the road. "I just don't -"

"What?" Jimmy prompts, after his sudden stop. "What is it?"

"I don't freaking believe it."

"What?" Jimmy follows his gaze, only to see a car - an old Chevy, black - pull up directly outside the house, before the driver, a guy about their age, in a plain sweater and jeans, all but jumps out, taking a moment to make sure that his sunglasses are perfectly straight on his face.

 _Sunglasses. Who the hell wears sunglasses in fucking autumn?_

"Hiya, Sammy." The guy leans up against the fence as he speaks, cocky grin stretched across his face. "Miss me?"

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 **Well, that's it for this chapter. Please don't hurt me. See you soon, my little sock puppets... ;) x**


	2. Say What?

_**2.**_ _Say What?_

"I still don't get it."

"What do you mean, you don't get it?" Jimmy glowers at Luke from across the room, the effect of the stern expression ruined by his hurried blinking in order to dislodge the sting from putting his contact lenses in, as Chuck tries to get the fake stubble spread evenly across his cheeks. He's been complaining about the arrival of the older Winchester ever since he and Gabe had left Sam's place that evening and got on the road for the next town over, the venue for the festive where Castiel had agreed to play. Mary, of course, had been thrilled to find out that her son had come home in order to finish his tour in Pontiac; Jimmy, on the other hand, not so much.

"He was rude," he continues, as Chuck gives his chin a final dab, before dropping the sponge back onto the table. "Plain and simple."

"He seemed alright to me," Gabe says, adjusting the baseball hat he's pulled on over his wig. When Castiel's identity had been created, it turned out that he did not come alone. He had brothers too - Gabriel and Lucifer, to name names.

"That's because he actually _spoke_ to you," Jimmy replies grimly. "You know, spoke to you with actual words, and didn't reply to your questions through condescending glances."

"You were the one asking him stupid questions about his sunglasses."

"Because who the fuck wears sunglasses _inside_?" Jimmy emphasises the word with a huff, grabbing Castiel's signature trenchcoat from the back of the couch (he'd worn it once whilst performing with the flu; now he can't get rid of it. People - Meg - sometimes got borderline angry when he was seen without it).

Gabe snorts. "Blind people?"

"Well, Dean didn't seem particularly _blind_ to me," the younger sibling grumbles, hands in his coat pockets, as he heads towards the door, and the corridor that will take him out to the stage. "I don't get it. So he can sing; that doesn't give him the excuse to be an assbutt."

"Sounds to me -" Luke says, sharing a smirk with Gabriel, slipping into a sing-song tone. "- like _somebody's a little jealous_."

"No, I'm not!" Jimmy insists, yanking the door open with more force than necessary. "And _stop singing_!" He makes sure to slam the door as well, if only to cut off the laughter coming from his brothers, before it suddenly opens again, and Chuck slips out.

"Better be careful that you don't knock the door off its hinges," he says, a slight smile on his face at his own joke. "I don't want the hassle of the paperwork if Castiel gets taken in for damage to property."

It's not that funny, but it still pulls a snort from Jimmy. "The press would have a field day."

"True. They would." Chuck pats his son on the shoulder, using his hand to guide him down the corridor, towards the sounds of the crowd, cheering on the current act. "So, this Dean -"

"Dad." Jimmy sends him a look. "Not you, too. I've heard his name too many times today already." He clears his throat, slipping into Castiel's gravelly tone, now that they're getting within the proximity of people not in the know. Better to be safe than sorry, after all (even if Jimmy's vocal chords didn't always agree.)

"He was so rude," he continues. "He didn't even ask our names."

"Maybe he was just happy to see his brother again after so long."

"There's a line between being happy to see your brother and just being an ass for the sake of it."

"Oh, I don't know. He didn't seem so bad. Not when I spoke to him -"

"Wait, wait, say what?" They come to a complete standstill. " _You_ spoke to him? When was this?"

"Uh -" Chuck finally drops the hand from his son's shoulder. "About, you know, an hour ago -"

"An -" Jimmy narrows his eyes. "Why were you -"

"There they are!" He's interrupted by the arrival of a redhead, who comes barrelling around the corner, only to throw herself into his unsuspecting arms. Jimmy glances up, more than a little confused, only to see Dean following the girl, a few paces behind her. Explains how Chuck had been talking to him earlier.

At least he's managed to remove the sunglasses. Jimmy isn't sure that he would have been able to restrain the urge to knock them from his face if he came in wearing them.

The redhead pulls back from the unexpected hug, grinning broadly. "Castiel. It's great to finally meet you in person." She looks him up and down. "I thought you'd be a little shorter, personally."

"Oh -" Jimmy exchanges a look with Chuck. "I, er - sorry to disappoint."

"Leave the guy alone, Charlie," Dean says, fondness in his tone, as he turns to "Castiel". "Sorry about her, man. Charlie's my boss; she can be a bit over excitable."

"Hey!" Charlie digs him in the ribs playfully, still beaming brightly.

"It's not a problem." Jimmy meets Dean's gaze to attempt to smile; Dean seems to blink rather rapidly, as if not realising what he's seeing, and, for a horrible impulsive moment, Jimmy is certain that he can see right through the fake stubble and messy hair that seem to fool nearly everybody else. But, then, the moment passes, and Dean smiles at him, holding out a hand for him to shake.

"Dean."

Jimmy exhales in relief. The last thing he needs is for Dean Winchester, of _all_ people, to work out who he really is. "Hello, Dean."

They share the proposed handshake.

"I've heard some of your music," Jimmy continues, after a moment, making an extra effort to make sure that his voice doesn't start to morph back to its usual tone. "You have a lot of talent."

Dean shakes his head, but there's a smile on his face still. "Kind of you man, but I'm the one who should be complimentin' you - y'know, startin' so young, and keepin' yourself on the ground, and everythin'. That's cool."

"Such a way with words," Charlie teases from beside him, before looking back to Jimmy. "But, we aren't just here to mingle and share feelings, Cas - Can I call you Cas?"

"Uh -" Yet again, Jimmy isn't entirely sure what to say. He's never been ambushed by people just before going on stage, not even by fans of Meg's level. "I don't see why not."

"Awesome! Well, anyway, Cas, me and your dad were just talking while you were getting ready, and we've been negotiating a few things."

"Oh?" Jimmy glances back at Chuck, who's looking a little too sheepish for his liking. "Such as?"

"Well..."

"Well?"

"We were thinking," Charlie says, when Chuck can't seem to make himself, "that it might be a good idea for you and Dean to collaborate." She emphasises this _good idea_ with another one of her bright smiles. Not that it does anything to reassure Jimmy.

"Colla - Say what?" He directs this towards his father. "When did you agree to this?"

"Hey, now -" Chuck holds up his hands. "We haven't agreed to _anything_ yet. We just think it would be a good thing for both of you."

"Good thing for - _Say what?_ "

"Castiel, we really don't have time to talk about this now." Chuck cuts him off with a look, that stern father expression he's perfected after having three children. "You're due on stage now; We'll discuss this when we get home, okay?"

"Hey, man, for what it's worth," Dean says, interrupting, still smiling, despite the exchange going on in front of him. "I'm up for it."

Well, great. How is he supposed to refuse after that without making himself look like a dick?

"No, no," he assures the other guy, although he's pretty sure the words are sliding through gritted teeth. "Don't worry - I'm _up for it_ too."

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 **Well, there's that :) See you soon, my little sock puppets :) X**


	3. The Other One

_**3.**_ _The Other One_

 _Duuuuuude! Where R U? Castiel_ _'s interview is being shown today & U promised U'd be here!_

Jimmy sighs as he reads the text from Meg, before tossing his phone to one side in favour of focusing on his guitar. He can't think of a convincing excuse to reply with right now; she's going to murder him regardless of what he tells her, out of anger at the fact that he hasn't shown up to her Castiel Interview Watching Party - or CIWP, as Sam and Amelia have dubbed it. Instead, he's dressed as aforementioned Castiel, in black slacks and a plain button down shirt, stubble expertly applied, sitting on the floor of one of the booths at the recording studio where Dean has agreed to meet him. He's already surrounded by screwed up pieces of paper, choruses and verses of different song lyrics that he's tried to formulate into whole songs, without much success. There's another collection of words on the current sheet of paper in front of him, the ones that he's trying to put a tune to whilst he waits, but it's not going so well.

"Wondered where you were hidin'."

Jimmy's head snaps up at the sound of the voice, only to see Dean peering at him through the glass, grinning. He reaches for the door handle, and walks in a moment later, now that Castiel has been startled.

"Was startin' to think you'd bailed on me," Dean continues, raising an eyebrow at the paper that crunches under his feet. "But apparently not. What's all this?"

"I was trying to come up with some song lyrics for our collaboration," Jimmy explains. "None of them were working."

"Really?" Dean sits down opposite him, cross-legged, reaching for one of the pieces of paper, and unfolding it, reading the words aloud. " _Would you put up resistance, would it make a difference, would you know the real me, me in my old blue jeans._ "

"I know. They suck."

"No way, man," Dean says, but Jimmy simply shakes his head, prompting him to discard the lyrics once more. "What'cha workin' on now?"

"I'm not really sure yet," Jimmy admits. "It's got more than what anything else I've written today has, but it's not finished."

"Huh," Dean says. "Can I hear it?"

"Uh -" Jimmy stumbles for a moment. Half of the lyrics of this thing - it's not a song yet - are his vented frustrations over the past day or so. Possibly not enough for Dean to recognise and make the connections, but, still, the risk is there. "I guess? Bear in mind, it's not finished, so there's still some gaps."

"That's cool." Dean rests his palms on his knees, an indication that he's ready and eager to listen. "Take it away, buddy."

"Right. Yeah. Um..." Jimmy shifts, plucking a few odd strings on his guitar, before carrying on with the soft melody he'd been playing before Dean arrived, pulling the sheet of paper towards him in order to reference.

 _When I walk in a room, everybody stops,_

 _Cameras flashing, people fighting for the best shot,_

 _They like my hair, the clothes I wear,_

 _Everybody wants to know what I'm doing next,_

 _Sometimes I wish I could stay home, just be by myself_

 _I want to be..._

He hums wordlessly in place of the missing lyrics, the ones that he hasn't thought of yet (or won't sing for fear of risking suspicion).

 _So you want to be just like, so you want to be just like,_

 _Think you want to be just like me,_

 _Everybody's watching me, it's not as easy as it seems,_

 _To be super, super, to be super, superman._

"Yeah, I know," Jimmy says, once he's finished singing. "It's kind of cheesy, but -"

"Cheesy can be good sometimes," Dean says, as if to reassure him. "If it comes from the heart."

"Thought you didn't do that sort of thing."

Dean raises an eyebrow, an amused smile on his face. "What made you think that?"

Jimmy opens his mouth to answer, before stopping. Dean himself had given him that idea, when they were all at the Winchester house only yesterday; the phrase "No chick-flick moments" had left Dean's mouth at least three times.

"Your music," he says finally, unable to come up with another answer. "Um, I think it's not as cheesy as my songs."

Dean snorts. "Dude, are you kiddin'? All of my music is cheesy, at least in the beginning, without any backin' track. Look at _True Friend_ , jeez. Sappiest shit I've ever written."

"That was my favourite. Says a lot, doesn't it?"

"Yeah. I wrote it about my brothers, a few years ago."

"You have brothers?" Jimmy asks, feigning ignorance.

"Two. Well, one half brother and one full brother, but, like Uncle Bobby always said, family don't end with blood. Adam and Sammy, they're called. Adam's only young, but Sammy's in college here in Pontiac, studyin' to be a lawyer - speaking of Sammy -" Dean reaches into his pocket suddenly, retrieving his buzzing phone, chuckling as he looks at the messages on the screen. "Looks like he's got friends over now I'm not there to embarrass him. God, I wish you could see them; they're the most mismatched bunch of people you could ever meet."

"Is that so?" Jimmy says; it's taking all of his acting skills to remain casual.

"Yeah, man. I mean, there's Sammy, obviously, then there's Meg, she's, like, your biggest fan, apparently, then Amelia, who seems to hate your guts - M'sure it's nothin' personal -"

"I'm sure." He can't quite keep the dryness out of his tone.

"And then there's Sammy's boyfriend, and his brother. Both of 'em are weird; Gabe is way too obsessed with pullin' pranks on people, an' the other one -"

"The _other one?_ "

Other one.

 _ **Other one**_.

 _Who the fuck does this guy think he is?_

"Yeah...er, Jim, or somethin', I think Sammy said. No matter; all he did was sit in the corner of the kitchen wearin' one of those dorky sweaters and snark -"

"It was _not_ dorky!" Jimmy says, indignant, before quickly regaining his composure. "I, uh, I rather like those sweaters."

Dean snorts. "Why doesn't that surprise me? I'm sure you and him would get on. Now -" He closes the subject, patting Jimmy on the knee, missing the glare that is being fired in his direction. "Are we gonna write a song, or what?"

* * *

 **Well, that was that :) See you soon, my little sock puppets... x**


	4. Bill

_**4.**_ _Bill._

"I can't believe we're doing this."

"Stop being so grouchy." Luke reaches over to his little brother, only to yank his beanie down over his eyes, making Jimmy protest. "You agreed to come, so don't start bitching about this now."

Jimmy glares at his brother, and grumbles quietly to himself under his breath, not really wanting to admit that his brother is right. Sam had begged and pleaded with his older brother until Dean had, rather unwillingly, agreed to give them VIP access to the last show of his tour, meaning that six of them are now crowded backstage whilst Dean himself runs through final vocal exercises, Gabe munching his way through the dessert table as he leans on Sam's shoulder. They look to be the happiest out of all of them, Jimmy feels. He's not even sure why he actually agreed to this in the first place. Dean doesn't even remember his fucking _name_ , after all.

Meg is pulling a face, sniffing at the view around her. "Look at this place."

"What's wrong with it?" Amelia asks, looking up from the book she's brought with her. She's decidedly as uninterested in the entire thing as Jimmy is.

"We've just been left here." She scowls. "Like _vermin_. Abandoned to run wild. My Castiel would never let his fans walk around in this squalor."

" _Your_ Castiel?" Jimmy repeats, as Amelia lets out a groan at the mention of Castiel's name, yet again.

"Yes, Jimmy. _My_ Castiel. My unicorn. My future husband. He has many titles."

"Future husband, eh?" Luke says, winking at his younger brother, prompting Jimmy to elbow him in the ribs. Luckily, he can't say anything else, for Dean has apparently finished his final vocal checks and wandered over to grace them with his presence, Sam and Gabe in tow.

"You guys havin' fun?"

"Oh, yeah, _buckets_ ," Jimmy says. He isn't as quiet as he intends, however, because Dean's gaze flickers over to him.

"Hey..." Jimmy watches as he tries for a smile. "Jim, right?"

"Jimmy."

"Close enough."

"Not really."

Gabe clears his throat, clearly trying to make some kind of silent point about manners. They've had this conversation already, Jimmy and he, multiple times, when he picked Castiel up from the recording studio and spent the entire ride home listening to his little brother ranting about how enraged he was at the fact that Dean couldn't be bothered to learn their names.

Jimmy takes the hint, and sighs. "Yeah, alright, close enough, I guess."

Dean raises an eyebrow, seemingly having picked up on his bad mood."You're, er, not really into this sort of stuff, are you?"

"You could say that." Jimmy exchanges glances with Gabe. "I'm more of an audience person."

"What sort of stuff do you like, then?"

"Huh?" Jimmy blinks; Dean repeats the question, more patient than he expected. "Why the hell would you want to know that?"

Dean shrugs, a smile on his face, a genuine one, not the fake politeness he had been putting on a moment ago. "Because I just do."

"Why? So you can make fun of me, or something?" He still hasn't forgiven the comment about the sweaters. In fact, he's even wearing one tonight, in order to prove a point.

Dean looks almost genuinely hurt. "You really think I'm that kind of guy?"

"Well, I don't know, do I? You didn't exactly _speak_ to me last time we met, did you?"

"Suppose not." Dean looks like he's about to say something different, perhaps defend himself, but a glare from Sam stop him. Jimmy wonders what kind of conspiracy his brother and the younger Winchester are running, because they seem to be in cahoots with each other.

"Think we really got off on the wrong foot, man." He holds out a hand, almost like a peace offering. "We should start over. Hi. I'm Dean."

Jimmy looks at the offered hand for a moment or two, debating whether or not he should stick to his original first impressions and simply leave, rather than get caught up in all of these complications. But, then again, it's already complicated as it is; Castiel still has to spend time with the guy, so maybe it might be better for everybody if he's on at least partially good terms with the elder Winchester.

In the end, he takes the hand. "Hi, Dean. I'm Jimmy." The youngest Novak raises an eyebrow. "So, what's brought on this sudden change of heart?"

"You're a friend of Sammy's, aren't you? A friend of Sammy's is a friend of mine. Besides, you kinda remind me of someone I met. We were talkin' about you, actually; Cas was very complimentary of your, er, sweaters."

"Wait, wait -" Meg interrupts suddenly, eager at any possible mention of her unicorn. "Cas? As in... _Castiel_?"

"Uh -" Dean frowns, as if realising what a horrible mistake he's just made in mentioning the singer by any kind of nickname. "Well, yeah, but -"

" _You met him?_ " Meg almost knocks Jimmy to the ground in her attempt to grab hold of Dean and look him directly in the eye. "What was he _like_?"

"Um, alright."

"Alright?" Meg repeats, incredulous.

"Alright?" Jimmy repeats, mildly offended.

"He was just normal, really. An ordinary guy." Dean shrugs.

 _Ordinary guy._

Jimmy makes a mental note of that. He could make a song out of that.

Meg, however, scoffs. "Ordinary? That's boring. C'mon, man, give me _details_. Is he as beautiful is real life as he is in pictures?"

"Er - well, I'm, um, not really the sort of guy you should be askin' -" Dean is suddenly looking anywhere but Meg's face, much to her annoyance, and Jimmy's bewilderment. "But, yeah - well, I mean, he ain't _bad looking_ , but, y'know, not - I mean, I don't swing that way, so who knows how handsome of a devil he is."

"Handsome?" Sam quotes, only to have Gabe snicker. Jimmy fires a glare at him, but no one sees it.

"Nothin' wrong with admittin' that another guy looks good, Sammy," Dean responds quickly, before turning back to Meg, moving swiftly on from her question. "But, yeah, I mean, he's just a weird, dorky little guy who likes to sing. Kinda like me, I guess, except I'm super cool, and all that."

"Eh, debatable," Meg says, wasting no time with moving on to her next question. "What did you guys talk about? Is Castiel his real name? Because I've seen theories -"

"Of course it's not his real name," Amelia says from behind them, rolling her eyes. "It's a stage name, and a fucking pretentious one, at that."

"You think so?" Jimmy asks. Maybe it is a little over the top, but he had only been sixteen when he started out, and the idea of being named after an angel seemed pretty cool.

"Definitely." Amelia wrinkles up her nose. "I bet his name is something really plain and basic in real life. Like...Charlie, or something. Or Bill."

" _Bill_ ," Meg repeats, almost dreamily, looking like she's about to faint just thinking about the possibility.

Jimmy catches Dean's eye. Both of them are trying not to laugh.

* * *

 **I hope you're all enjoying this so far! Until next time, my little sock puppets... :) X**


	5. Anytime, Sweetheart

_**5.**_ _Anytime, sweetheart_

Castiel may be a successful pop star, but the real world doesn't stop turning for Jimmy Novak. He still has college, after all - classes to go to, assignments to turn in, lunch to eat, etcetera. Sam and Gabe put forward the idea of setting up some kind of band, now that the Halloween talent show is coming up and none of them ever participated in something like that during high school. Although, Jimmy suspects, Gabe no doubt planted the idea in order to tease his little brother, and so, for that reason, he politely declines to be involved. He has enough to deal with right now, almost all of it Castiel-related.

"Sometimes it really does feel like I'm more Castiel than I am myself," he says offhandedly to Luke one day, picking at a sandwich in front of him.

Even though he's halfway out of the door, Luke still finds the time to roll his eyes at his younger sibling.

"You chose this, dumbass. You knew what would happen if your career took off, and it did. You can't undo it now."

"I never said that I wanted to undo it," Jimmy replies. He loves being Castiel; after all this time, the guy feels like the phantom twin brother he never got to have. "It's just sometimes I wish I had more time to myself, you know? I'm always out doing a signing, or a concert, or I'm studying with the others, or, I don't know, something. It would be nice to lay in bed for a while and just...you know, _be_. For a change."

Luke considers this, before shrugging. "Hey, don't worry about it, Jim-Jim. Just think, in a few years, Castiel will a faded star of the music industry, gone and forgotten; you'll have plenty of time for your mid-youth crisis there."

Jimmy levels him with a resigned look. "Thanks, Lukey."

"Anytime, sweetheart." His brother gives him a two-finger wave as he saunters off, leaving Jimmy alone in the kitchen to ponder over the remainder of his sandwich. He doesn't get to ponder for very long, however; a few seconds later, the phone on the counter starts buzzing, the number unknown. Jimmy has never been one to follow the obvious course of action, however, and so answers anyway, tearing a chunk of bread and cheese with his teeth.

"Novak residence."

"Hey, man!" The familiar voice echoes down the line. "Just the guy I was lookin' for."

Jimmy almost chokes on his mouthful. "Dean? Dean Winchester?" _Well, this is unexpected._ "You, er, you know it's Jimmy, right? Do you want me to get Gabe, or - ?"

"No, no, man! It _is_ you I wanna speak to."

"Um. Alright." The sandwich is forgotten, in favour of Jimmy directing his confused expression at the tabletop in front of him. "What can I do for you?"

"I kinda..." Dean trails off. "See, I've got this stuff goin' on - like, personal, I don't know, crap, right? And I was hopin' -"

"If you've gotten yourself mixed up in drugs, I'm not bailing you out," Jimmy interrupts dryly.

Dean snorts. "God, no, nothin' like that. Hell, Mom wouldn't put up with that in her house. Nothin' incriminatin', cross my heart. S'just stuff I don't really want to talk to Sammy 'bout - brothers, you know how it is."

"True." There are many things he refuses to discuss with family, especially around Gabe. He loves his brothers, dearly, but he knows that there is a high chance that things will find their way back to Chuck one way or another, and once Chuck Novak got a sniff of something, he would never let it go. "Alright. This had better be quick, though, Dean; I've got an appointment." Well, _Castiel_ has an appointment. With Dean, in the recording studio, no less. "What is it you wanted to talk about?"

He hears Dean suck in a breath, preparing himself. "Jim...how do I tell this person that I like them?"

There's a pause, before Jimmy snorts. "Wh - Seriously? Dude, this isn't the ninth grade. Just tell them how you feel. Be straight with them."

" _Straight_ ," Dean repeats, with a humourless chuckle, the sound almost breathless. "Oh, the irony, man."

It takes a moment to click. "Oh. I see."

"Yeah. I'm, uh, battin' for both teams here, if you know what I mean. Not somethin' I really like to talk 'bout."

"Why?" Jimmy wrinkles up his nose to match his tone. "Nothing wrong with it. Hell, I bat for the same team, if you wanna put it like that, and I'll talk about it if people ask."

"Really?" He can practically see Dean relaxing in his mind.

"Yeah." Jimmy prods the sandwich - he's just remembered that it's there - before he picks the plate up and dumps the food in the garbage. "So, come on. Girl or guy?"

"Guy."

"Nice." He deposits the plate too, making his way towards the stairs. He has to head to his room to change into Castiel's usual attire, a shirt and some slacks, as opposed to the brightly coloured band t-shirt he's wearing now. "What's he like?"

"God. How long have you got, 'cause I could go on and on, buddy. He's small, and cute, and so talented - but not one of those asshole kind of talented people. He's so down to earth, and soulful, and just -" He cuts himself off. "Sorry. M'not - I don't usually do chick-flick moments."

"It's okay." Jimmy keeps the phone pressed to his ear as he flails with the sleeves of the shirt. "It's kinda cute, not gonna lie."

"Shut up," Dean replies, but Jimmy is fairly sure that there's a smile there.

"What I don't understand, though, is why you wanted to ask me about it."

"Sammy and Adam - I mean, I love them, don't get me wrong, but it's just kinda awkward talkin' about this sort of stuff with them. Besides, wherever Sammy is, your brother is there too, so that rules that out. I'm not havin' Gabe hearin' about this; I'll never hear the end of it."

"Good point. I know, from nineteen years of experience, that this is true."

"Exactly. And Mom - well, she's supportive of everythin' I've done so far, but I don't really wanna sit down at the dinner table and discuss this stuff. Which just left you, really."

"I'm glad you gave me such consideration." Jimmy huffs, partly from the remarks and partly from the effort of trying to dress and maintain a conversation. "Ass."

"Shut up, you son of a bitch, I didn't mean it like that." Dean is no doubt rolling his eyes. "But, yeah, enough 'bout that. How am I supposed to let this guy know - well, you know."

"Christ, Dean, you know you can say the words _I'm into him._ They will not kill you." Now it's Jimmy's turn to roll his eyes, pulling his glasses off and throwing them unceremoniously onto the bed. Thank God he doesn't constantly need them, or it would be much harder to navigate his double life. "Why don't you just ask him to hang out sometime or something? Start with...I don't know, start with a burger or something? I'm not fucking Cupid."

They wrap the conversation up pretty quickly after that, Jimmy making his getaway due to his appointment excuse. He wonders, during the fifteen minute car journey, who exactly could of caught the attention and affections of none other than Dean Winchester. Well, whoever they were, God had better be with them; Jimmy hasn't known Dean for long, and already he's not sure what to think of him anymore. What person calls the house of a person whose name they can barely remember, before proceeding to have some kind of deep conversation with them about sexuality and crushes?

Honestly, Jimmy half preferred it when it was just a week ago, and Dean Winchester was just Sam's asshole older brother who wore sunglasses in the middle of fucking autumn.

Aforementioned sunglasses-wearing asshole brother (who isn't as much of an asshole as before) is sitting in the middle of the recording booth when Jimmy eventually makes it inside, Castiel's unshaven stubble hastily applied in the car with his fingers. He brightens up when he sees the sight of the other singer, like a kid who's just spotted their parents watching them in their elementary school Christmas performance. Completely different from the Dean Winchester he had been speaking to on the phone half an hour before.

"Hey, Cas!"

"Hello, Dean," he greets, taking a seat beside him. "What have you been up to in here?"

"I was just messin' around," the other man begins, pulling his iPod out of his leather jacket, juggling it in his palms, "and I figured we should be gettin' some inspiration for this collaboration."

"Right," Jimmy replies, sounding more suspicious by the minute. "What exactly does that entail?"

"I downloaded a bunch of songs, both of ours, and I figured we should listen to them. You know, take bits we like, bits we need to avoid -" He raises an eyebrow. "Yeah?"

"This is so embarrassing."

"Stop whinin', Cas." Dean drops in the eyebrow in favour of rolling his eyes, as he plugs his iPod into the studio speaker without anymore hesitation. "Do you know who whines? Babies."

Jimmy sticks his tongue out at him. "Do we really have to go all the way back to the beginning? These old songs are so cringe-worthy."

"They made you who you are today, didn't they?" Dean says, before chuckling at the put-out expression he gets in response. "Don't worry, we're gonna take it in turns; we're gonna hear all of my early stuff too."

"Great," Jimmy says sarcastically, only to feel himself wincing, ready to curl in on himself in his seat as the opening chords of his first song start to blast out of the speakers, along with Castiel's sixteen-year-old voice.

 _By day, I play,_

 _The part in every way,_

 _Of simple, sweet, calm and collected,_

 _Pretend, to my friends,_

 _I'm a chameleon,_

 _Can make a guy feel disconnected._

"Oh, _God_ -"

"Aw, c'mon, man, it's cute! _Feel like a star, a superhero -_ "

"Stop it, assbutt."

Dean laughs at the petulant expression, before clearing his throat, cutting the sound off. "Hey...Hey, Cas?"

"Yes?" Anything for a distraction from these cringy lyrics, Jimmy thinks; _Sometimes it's hard to separate, got too much on my plate._

"Do you, um -" Dean looks away, at some poky corner of the ceiling, before picking at the zip on his jacket and sighing. Jimmy could almost say that he looks nervous. "Do you want to go out after this?"

 _If you could see,_

 _The other side of me,_

Jimmy blinks. "Y - Say _what_?"

 _I'm just like everybody else,_

 _Can't you tell?_

"Like, nothing too fancy. Just for a burger? My treat?" Dean's back to looking at him now, apprehension starting to bloom in his green eyes. "I mean, you don't have to - I just thought -"

"It's fine," Jimmy says, although whether it's to reassure Dean or to reassure himself he isn't sure.

Dean freaking Winchester is asking him out for a burger.

No, Dean freaking Winchester is asking _Castiel_ out for a burger, after asking _Jimmy_ how to ask a guy out.

 _Oh, shit._

"So, what d'you say, Cas?"

 _The guy that I want you to know,_

 _If only I could show,_

"I -" Jimmy begins, but he can't think of the right words, to try and ask Dean what the hell this means. He could (unlikely) just be blowing the whole thing out of proportion. Maybe Dean is just testing the waters? Putting advice into practise? It is just a burger, after all - and, if this is what he thinks it is, he can just defuse the situation, right? Right.

"Alright," he says finally, as the end of the chorus of _The Other Side of Me_ blares out of the speakers. "Just for a burger."


End file.
